Triethylamine → HCID 14851908, compound

HRID 1032788Notes

Reaction equation

HRID 1032788 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16](I)[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[CH2:27]([N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])[C:28]#[CH:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:29]#[C:28][CH2:27][N:30]3[C:34](=[O:35])[C:33]4[C:32](=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:31]3=[O:40])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 81644N-prop-2-ynylphthalimideHCID 14851909HCID 14851909, compound

Product 1

HCID 14851908HCID 14851908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.94 g (2 mmol) of 6-(2-fluorophenyl) 8-iodo-1-(trifluoromethyl)-4H-[1,2,4]triazolo [4,3-a][1,4]-benzodiazepine, 0.55 g (3 mmol) of N-propargylphthalimide 80 mg of triphenylphosphine, 20 mg of cuprous iodide, 0.6 ml of triethylamine and 50 ml of dimethylformamide was degassed with argon for 10 minutes. Palladium acetate, 25 mg. was then added and the mixture was stirred for 3 days at room temperature. The product was precipitated by dilution with sodium bicarbonate solution and was collected by filtration. It was dissolved in methylene chloride and the solution was washed with bicarbonate solution, dried and evaporated. The residue was chromatographed over 40 g of silica gel using 5% (v/v) of ethanol in methylene chloride. The combined good fractions were evaporated and the residue was crystallized from ethyl acetate to give colorless crystals of 2-{3-[6-(2-fluorophenyl)-1-(trifluoromethyl)-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepin-8-yl]-2-ProPynyl}-1H-isoindole-1,3(2H)-dione with m.p. 204°-206° .

Workup

  1. customwas degassed with argon for 10 minutes
  2. additionwas then added
  3. customThe product was precipitated by dilution with sodium bicarbonate solution
  4. filtrationwas collected by filtration
  5. dissolutionIt was dissolved in methylene chloride
  6. washthe solution was washed with bicarbonate solution
  7. customdried
  8. customevaporated
  9. customThe residue was chromatographed over 40 g of silica gel using 5% (v/v) of ethanol in methylene chloride
  10. customThe combined good fractions were evaporated
  11. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2638f361e377485db64477bcaf0eac56
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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